I've lived in Colorado Springs for a few years so here are a few suggestions...A nice hotel in the downtown area is The Mining Exchange. My in-laws stay there when they are in the area and our guest room is already occupied. It is a cool hotel with a lot of history. I think the nicest hotel in the area is probably The Broadmoor, I haven't stayed there personally. There are quite a few nice restaurants in the downtown area and a few breweries. Phantom Canyon is a nice brewery in the downtown area and the food is pretty good too. Nice building with an upstairs area with some good views of the mountains. Other downtown area restaurants that are very popular and good are The Rabbit Hole, King's Chef Diner, Jack Quinn's Irish Pub, Mackenzie's Chop House, and The Melting Pot. I would recommend getting reservations at all of these places (Except King's Chef, not sure they do reservations).
Over on the west side, we have some fantastic Italian food at Paravicini's Italian Bistro (best Italian in town). Other favorites include a Greek/Mediterranean restaurant called Jake and Telly's, Garden of the Gods Gourmet, amazing breakfast/lunch at Bon Ton's Cafe, and decent bbq at Front Range BBQ. If you like Sushi, Nara Sushi is pretty solid. I make all my own bbq so I don't really eat at any BBQ joints in Colorado Springs, not really anything like Texas BBQ. Definitely AVOID Bird Dog BBQ...just not good at all.
There are breweries all over the place, some have great beer and not so great food. Bristol Brewery is an old Elementary school building that has been converted into a brewery. Cool place, good beer, food sucks. Colorado Mountain Brewery at the Roundhouse (west side) has some good beer and some pretty good food, but it's more of a commercialized place. Red Leg brewing Co has good beer, veteran owned and operated. There is a really cool relatively new brewery called Trails End Taproom that has a ton of beers and is a self-pour taproom, great for the beer lover. You basically put money on a card and swipe it at each tap and the beer is priced per ounce, so you can try as little or as much as you want. Cool concept. Another cool pub is called Pub Dog. First bar that is dog friendly (dogs allowed inside). Good food and beer/drinks. And then of course Phantom Canyon Brewery as mentioned earlier.
Cool things to do, check out Garden of the Gods if you want to deal with a ton of people. Its probably worth driving through, but can get pretty crazy with other tourists. There is a train ride called the Pikes Peak Cog Railway. Scenic train ride up to the top of Pikes Peak. To get to the station where the ride starts you have to drive through Manitou Springs which is west of Colorado Springs and a pretty cool little town to walk around.
There are some cool Museums in town. The Ghost Town Museum, the National Museum of WWII Aviation, the Colorado Springs Pioneers Museum, up north (by the Bass Pro) is the Western Museum of Mining & Industry, there is also the Pro Rodeo Hall of Fame. Other cool things to see are west of Colorado Springs near Manitou Springs is the Manitou Cliff Dwellings, and the Cave of the Winds. If the kids like dinosaurs, might check out the Rocky Mountain Dinosaur Resource Center in Woodland Park. Its about a 30 min drive from Colorado Springs.
There are also tons of hiking trails in and around Colorado Springs. Some easier than others but if you are active and enjoy hiking they are a lot of fun and have some great views, little waterfalls/creeks etc. I can suggest a few if you are interested. If you have any other questions I may be able to help with feel free to ask or PM me!